40 Flirty Questions to Ask a Guy and Leave Him Thinking of You

Want to start something, but aren’t sure how to go about it? These flirty questions to ask a guy are the perfect start to leave him thinking of you.

flirty questions to ask a guy

It’s hard when you like a guy. You want to chat but are either too nervous to pluck up the courage, frightened you’ll run out of things to say, or worried your conversation will end up boring. Maybe you come across as too friendly instead of flirty. But these flirty questions to ask a guy will put you on the right track.

Showing a guy your interest in him is a little nerve wracking. One of the less scary ways to do it is by striking up a flirty conversation with him. You don’t have to be too forward or risky, just ask some silly, funny, flirty questions and see where the conversation takes you. More importantly, see if he starts flirting with you too.

If he responds in kind then you know you are onto a winner. If he doesn’t then it’s not too late to back out gracefully without feeling like you got too much egg on your face! [Read: 15 easy ways to flirt with your crush]

40 flirty questions to ask a guy

How do you ramp up the conversation so it’s flirty rather than friendly? You want to take that next step and give him an indication you like him, but how?

If you want to start a flirty conversation with a guy you are in luck. Here we’ve compiled a great list of 40 flirty questions to ask a guy!

#1 Have I seen you here before? Even if you haven’t, this old ‘do you come here often’ classic is an obvious sign you want a flirty conversation. [Read: 40 unbelievably cute things you can say to your crush]

#2 Have you been working out? Asking a guy this is obviously telling him you’ve checked him out, and you think he looks good! [Read: 10 flirty moves girls think are cute but guys hate]

#3 Do you have a girlfriend? This question is pretty forward but it lays your cards on the table. It makes it pretty obvious to a guy you want to be more than just friends, right from the outset. Some guys think that kind of bravery is pretty sexy!

#4 Do you prefer cuddling up or having a make-out session? Putting pictures in his head of what it might be like to cozy up to you or to lock lips is a good indication you like him and want things to get flirty.

#5 Are you a cat or a dog person? Everyone knows if you ask this question it’s because you want to find out whether you are compatible. But if you are a cat person and they are not, it’s doomed!

#6 Why don’t you tell me more about yourself? This is a little bit subtler but is still a flirty question because it demonstrates your interest in them and the fact that you would really like to get to know them better.

#7 What’s the best kiss you’ve ever had? Asking a guy to reminisce about a hot kiss that he’s had will turn his mind to sex. Or perhaps you kissed already and you hope that he says you?! [Read: 40 crazy things to ask a guy and leave him falling for you]

#8 Have you ever had sex in an interesting/funny/risky place? Again, turning the conversation to sex tells him that you like him and are interested in finding out more about his sexual history. If he’s up for revealing things about himself and asks you the same, it looks like some serious flirting is about to begin!

#9 What’s your type? Now find out what he goes for, is it you?

#10 What do you find hot in a girl? If he starts describing you, you know you are onto a winner! [Read: Does he like me? 18 signs to decode a guy’s body language]

#11 How can you be single? Here you obviously tell him that you think he’s great and would sweep him right up off that singles shelf in a heartbeat.

#12 How did you get to be so cute? This question is cute and flirty without being too forward, if he likes sweet and cheeky girls he’ll love the compliment and give you one back right away!

#13 Do you think about me when we’re not together? Asking him whether he ever thinks about you is an easy opener for him to flatter you and make you feel great.

#14 What’s your ideal date? Get him to think about dating and hopefully he’ll picture you there with him.

#15 Are you busy on… ? This is a good way to get him to ask you out without being too direct.

#16 What’s your stance on a girl making the first move? Here you pretty much tell him you’ll make a move on him if he wants you to. It’s also an easy way for him to let you down if he doesn’t feel the same way.

#17 Do you ever get shy around me? If he does he’ll probably blush and stutter. It will be oh-so-adorable!

#18 Do I make you nervous? This is the same sort of question. If he says yes, tell him he makes you kind of nervous too. [Read: How to flirt with a shy guy and get him to open up to you]

#19 What turns you on? Again, if you want to be a bit forward, turn the conversation to sex and see where it takes you.

#20 What turns you off? Knowing the kind of things that turn him off will no doubt be useful later!

#21 Are you attracted to me? If you want to be flirty but also want answers, this question goes straight to the point!

#22 What do you wear in bed? If he responds with something normal, tell him you sleep naked and see what his response is!

#23 Do you want to go out with me? If you are the kind of girl that doesn’t like to beat around the bush, why not just ask him out already?!

#24 Do you fancy me? Ask him if he’s attracted to you—go on, we dare you!

#25 Have you ever had a dream about me? This cute question is a fun way to find out if he has you on his mind a lot, And if it’s a sexy dream, all the better!

#26 Have you ever had a sexual fantasy about me? Asking about his fantasies seems personal, but it’s a sure-fire way to know if he’s got the hots for you too. [Read: 16 naughty deeds to help build your sexual wish list]

#27 Do I make you smile? If he tells you that you make him laugh and then he obviously crushes on you big time.

#28 Do you know that you make me smile when I think about you? Watch his body language to clue if he likes you back or not.

#29 Are you a shy guy? If he gets shy around you, chances are he fancies you.

#30 What’s your favorite position? Find out what his favorite positions are in the bedroom and perhaps you can impress him later. [Read: 36 really racy and flirty questions for naughty guys and girls]

#31 What’s the most outrageous thing you’ve done in bed? See how wild he can be!

#32 Where’s your favorite make-out spot? Find out and suggest you go there pronto!

#33 What do you value in a relationship? See if you are compatible by finding out what’s important to him in a relationship.

#34 What do you like about me? Open the door for him to give you compliments. Then sit there and bask in the glory! [Read: Decoding compliments and understanding their true meaning]

#35 What’s your ultimate fantasy? Find out what he’s always wanted to do, and then make his dreams come true.

#36 What excites you? Find out what his passions are *not just sexually*. It leads to a bonding conversation and makes him feel more connected to you.

#37 What are your dreams? Find out if you dream about the same kind of future—hopefully one together!

#38 Do you think you know what women want? This is a way to get him all flustered. Then you tell him EXACTLY what you want

#39 Can you look after me? Make him feel all manly and protective by playing the damsel in distress. [Read: 21 ways to charm a guy and make him fall for you]

#40 If we went on a date how would it go? Getting him to imagine himself on a date with you increases the chances of it happening for real!

[Read: Wonder what exactly is flirting? Understand the science behind it]

These 40 flirty questions to ask a guy are what you need. So, next time you see your crush, and you feel ready to try some flirting, use the questions from this list. You’ll have a fun, flirty conversation going in no time at all!

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Bethany Locke
Bethany was born and raised in Scotland and now resides in Brighton where she lives with her partner and rather disobedient cocker spaniel pup. She works as a f...
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